Department of Chemistry

Prof Ross W. Boyle

BSc (Paisley), PhD (Paisley)

Ross Boyle

Professor in Biological Chemistry

Department of Chemistry

  • Profile
  • Teaching
  • Research
  • Key publications

Profile

Ross gained his BSc in chemistry from Paisley College, Scotland, in 1986, and remained in Paisley for his PhD in organic photochemistry under the supervision of George Truscott. In 1990 he moved to Canada where he carried out postdoctoral research, first at the MRC Group in Radiation Sciences, Universite de Sherbrooke, Quebec, with Johan van Lier, and then at University of British Columbia, Vancouver with David Dolphin. In 1996 Ross returned to the UK to take up the post of Lecturer in Biological Chemistry, at University of Essex, and in 2000 moved to his present post as Reader in Biological Chemistry, University of Hull.

Departmental responsibilities

  • Head of Molecules for Health Section
  • Chair of Postgraduate Student Committee
  • Research Committee Member
  • Staff & Estates Committee Member
  • Disabilities Officer

University responsibilities

  • Clinical Biosciences Steering Committee Member
  • Bioethics Committee Member

Teaching

Lectures courses

  • Structure & Synthesis I: Benzene Chemistry
  • Structure & Synthesis II: Heteroaromatic Chemistry
  • Biological Macromolecules: Porphyrins and Related Macrocycles
  • Advanced Organic Chemistry: Retrosynthetic Analysis
  • Topics in Molecular Medicine: Photochemistry and Photobiology

Laboratory classes

  • Advanced Organic Chemistry

Teaching interests

  • Organic Chemistry

Research

Research theme: Biological Chemistry
Research group: Photobiology and Photomedicine Group

My major interest is in the synthesis and applications of light active molecules, primarily in the area of biomedical science. My research group works closely with biomedical scientists and clinicians on an emerging cancer treatment called photodynamic therapy (PDT). PDT involves the administration of a tumour selective drug that is not toxic until activated by light of a specific colour, usually red. The ability to selectively activate the drug in the tumour avoids many of the side effects associated with chemo- and radiotherapy.

In a related area we are synthesising novel photoactive nanoparticles, which can be used to study the effects of reactive oxygen species (ROS) in cells. ROS are implicated in ageing, carcinogenesis, heart disease and Alzheimer’s disease.

Techniques routinely used in my research include organic synthesis, UV-visible and fluorescence spectroscopy, bioconjugation, tissue culture and fluorescence microscopy.

Since moving to Hull my research has received generous funding from EPSRC, BBSRC, Wellcome Trust, Leverhulme Trust, EU and the Royal Society.

Research interests

  • Synthetic chemistry of porphyrins and related molecules
  • Photodynamic therapy of cancer and other diseases
  • Fluorescent probes
  • Conjugation of photoactive species to biomolecules

Key publications

Porphyrin-nanosensor conjugates. New tools for the measurement of intracellular response to reactive oxygen species, L. B. Josefsen, J. W. Aylott, A. Beeby, P. Warburton, J. P. Boyle, C. Peers, and R. W. Boyle, Photochem. Photobiol. Sci., 2010, 9, 801-11. doi: 10.1039/c0pp00004c

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives, S. Jha, J. D. Silversides, R. W. Boyle, and S. J. Archibald, Crystengcomm, 2010, 12, 1730-9. doi: 10.1039/b924683e

Site-Specific and Stoichiometric Conjugation of Cationic Porphyrins to Antiangiogenic Monoclonal Antibodies, C. M. A. Alonso, A. Palumbo, A. J. Bullous, F. Pretto, D. Neri, and R. W. Boyle, Bioconjugate Chem., 2010, 21, 302-13. doi: 10.1021/bc9003537

Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity, Y. Zorlu, M. A. Ermeydan, F. Dumoulin, V. Ahsen, H. Savoie, and R. W. Boyle, Photochem. Photobiol. Sci., 2009, 8, 312-8. doi: 10.1039/b817348f

Full publications list

Porphyrin-nanosensor conjugates. New tools for the measurement of intracellular response to reactive oxygen species, L. B. Josefsen, J. W. Aylott, A. Beeby, P. Warburton, J. P. Boyle, C. Peers, and R. W. Boyle, Photochem. Photobiol. Sci., 2010, 9, 801-11. doi: 10.1039/c0pp00004c

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives, S. Jha, J. D. Silversides, R. W. Boyle, and S. J. Archibald, Crystengcomm, 2010, 12, 1730-9. doi: 10.1039/b924683e

Site-Specific and Stoichiometric Conjugation of Cationic Porphyrins to Antiangiogenic Monoclonal Antibodies, C. M. A. Alonso, A. Palumbo, A. J. Bullous, F. Pretto, D. Neri, and R. W. Boyle, Bioconjugate Chem., 2010, 21, 302-13. doi: 10.1021/bc9003537

Glycerol and galactose substituted zinc phthalocyanines. Synthesis and photodynamic activity, Y. Zorlu, M. A. Ermeydan, F. Dumoulin, V. Ahsen, H. Savoie, and R. W. Boyle, Photochem. Photobiol. Sci., 2009, 8, 312-8. doi: 10.1039/b817348f

Reductive Amination - A Convenient Method for Generating Diverse, Mono-Functionalised 5,10,15,20-Tetraphenyl Porphyrins, C. Welch, S. J. Archibald, and R. W. Boyle, Synthesis-Stuttgart, 2009, 551-6. doi: 10.1055/s-0028-1083335

Synthesis and phototoxicity of polyethylene glycol (PEG) substituted metal-free and metallo-porphyrins: Effect of PEG chain length, coordinated metal, and axial ligand, R. E. Mewis, H. Savoie, S. J. Archibald, and R. W. Boyle, Photodiagnosis Photodyn. Ther., 2009, 6, 200-6. doi: 10.1016/j.pdpdt.2009.08.002

Mesogenic dipyrrins - building blocks for the fabrication of fluorescent and metal-containing materials, C. J. Wilson, L. James, G. H. Mehl, and R. W. Boyle, Chem. Commun., 2008, 4582-4. doi: 10.1039/b806672h

Photodynamic therapy: novel third-generation photosensitizers one step closer?, L. B. Josefsen and R. W. Boyle, British Journal of Pharmacology, 2008, 154, 1-3. doi: 10.1038/bjp.2008.98

Development and characterization of novel photosensitizer : scFv conjugates for use in photodynamic therapy of cancer, C. Staneloudi, K. A. Smith, R. Hudson, N. Malatesti, H. Savoie, R. W. Boyle, and J. Greenman, Immunology, 2007, 120, 512-7. doi: 10.1111/j.1365-2567.2006.02522.x

Isothiocyanato-calix[4]phyrin-(1,1,1,1): a useful intermediate for the synthesis of derivatised anion sensors, S. C. Jha, M. Lorch, R. A. Lewis, S. J. Archibald, and R. W. Boyle, Org. Biomol. Chem., 2007, 5, 1970-4. doi: 10.1039/b703646a

Synthesis and in vitro investigation of cationic 5,15-diphenyl porphyrin-monoclonal antibody conjugates as targeted photodynamic sensitisers, N. Malatesti, K. Smith, H. Savoie, J. Greenman, and R. W. Boyle, Int. J. Oncol., 2006, 28, 1561-9. doi:

Isothiocyanato boron dipyrromethenes - The first BODIPY analogues of fluorescein isothiocyanate, N. Malatesti, R. Hudson, K. Smith, H. Savoie, K. Rix, K. Welham, and R. W. Boyle, Photochem. Photobiol., 2006, 82, 746-9. doi: 10.1562/2005-01-10-ra-769

Synthetic routes to porphyrins bearing fused rings, S. Fox and R. W. Boyle, Tetrahedron, 2006, 62, 10039-54. doi: 10.1016/j.tet.2006.08.021

Development of phage derived scFv : porphyrin conjugates for use in photodynamic therapy of cancer, C. Staneloudi, K. A. Smith, R. Hudson, N. Pesa, H. Savoie, R. W. Boyle, and J. Greenman, Immunology, 2005, 116, 35-. doi:

The development and characterisation of porphyrin isothiocyanate-monoclonal antibody conjugates for photoimmunotherapy, R. Hudson, M. Carcenac, K. Smith, L. Madden, O. J. Clarke, A. Pelegrin, J. Greenman, and R. W. Boyle, Br. J. Cancer, 2005, 92, 1442-9. doi: 10.1038/sj.bjc.6602517

Near IR emitting isothiocyanato-substituted fluorophores: their synthesis and bioconjugation to monoclonal antibodies, W. B. Duan, K. Smith, H. Savoie, J. Greenman, and R. W. Boyle, Org. Biomol. Chem., 2005, 3, 2384-6. doi: 10.1039/b504334d

Synthesis and structural characterisation of novel bimetallic dipyrromethene complexes: rotational locking of the 5-aryl group, J. M. Sutton, E. Rogerson, C. J. Wilson, A. E. Sparke, S. J. Archibald, and R. W. Boyle, Chem. Commun., 2004, 1328-9. doi: 10.1039/b404147j

Characterisation of Novel Porphyrin-Antibody Conjugates for Use in Photoimmunotherapy of Cancer, K. A. Smith, N. Pesa, V. Staneloudi, J. Swann, R. Hudson, H. Savoie, R. W. Boyle, and J. Greenman, Anticancer Res., 2004, 24, 480. doi:

Ultrastable complexes for in vivo use: a bifunctional chelator incorporating a cross-bridged macrocycle, E. A. Lewis, R. W. Boyle, and S. J. Archibald, Chem. Commun., 2004, 2212-3. doi: 10.1039/b406906d

Efficient N- and C-functionalisation of cyclam macrocycles utilising bisaminal methodology, E. A. Lewis, C. C. Allan, R. W. Boyle, and S. J. Archibald, Tetrahedron Lett., 2004, 45, 3059-62. doi: 10.1016/j.tetlet.2004.02.108

Strategies for selective delivery of photodynamic sensitisers to biological targets, R. Hudson and R. W. Boyle, J. Porphyrins Phthalocyanines, 2004, 8, 954-75. doi:

First examples of intramolecular Pd(0) catalysed couplings on ortho-iodinated meso-phenyl porphyrins, S. Fox and R. W. Boyle, Chem. Commun., 2004, 1322-3. doi: 10.1039/b403466J

Thioglycosylated cationic porphyrins - convenient synthesis and photodynamic activity in vitro, S. Ahmed, E. Davoust, H. Savoie, A. N. Boa, and R. W. Boyle, Tetrahedron Lett., 2004, 45, 6045-7. doi: 10.1016/j.tetlet.2004.06.021

Parallel synthesis of unsymmetrically substituted tetraphenyl porphyrins on Wang resin, B. L. Shi, M. Scobie, and R. W. Boyle, Tetrahedron Lett., 2003, 44, 5083-6. doi: 10.1016/s0040-4039(03)01142-0

Use of orthoesters in the synthesis of meso-substituted porphyrins, S. Fox, R. Hudson, and R. W. Boyle, Tetrahedron Lett., 2003, 44, 1183-5. doi:

Porphyrin, chlorin, and bacteriochlorin isothiocyanates: Useful reagents for the synthesis of photoactive bioconjugatest, J. M. Sutton, O. J. Clarke, N. Fernandez, and R. W. Boyle, Bioconjugate Chem., 2002, 13, 249-63. doi: 10.1021/bc015547x

Synthesis of unsymmetrically substituted meso-phenylporphyrins by Suzuki cross coupling reactions, B. L. Shi and R. W. Boyle, J. Chem. Soc. Perkin Trans. 1, 2002, 1397-400. doi: 10.1039/b201622b

First synthesis of porphyrin-phthalocyanine heterodimers with a direct ethynyl linkage, J. M. Sutton and R. W. Boyle, Chem. Commun., 2001, 2014-5. doi:

A C-13 NMR spectral examination of alpha- and beta-carbon signal peak heights in some disubstituted arylporphyrins, S. J. Shaw, S. Shanmugathasan, O. J. Clarke, R. W. Boyle, A. G. Osborne, and C. Edwards, J. Porphyrins Phthalocyanines, 2001, 5, 575-81. doi:

Photosensitisation of pancreatic tumour cells by a series of delta-aminolaevulinic acid (ALA) esters, C. J. Whitaker, S. H. Battah, M. J. Forsyth, C. Edwards, R. W. Boyle, and E. K. Matthews, British Journal of Pharmacology, 2000, 129, 89P. doi:

Photosensitization of pancreatic tumour cells by delta-aminolaevulinic acid esters, C. J. Whitaker, S. H. Battah, M. J. Forsyth, C. Edwards, R. W. Boyle, and E. K. Matthews, Anti-Cancer Drug Des., 2000, 15, 161-70. doi:

Functionalized diphenylchlorins and bacteriochlorins: their synthesis and bioconjugation for targeted photodynamic therapy and tumour cell imaging, J. M. Sutton, N. Fernandez, and R. W. Boyle, J. Porphyrins Phthalocyanines, 2000, 4, 655-8. doi:

Regioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin, S. Shanmugathasan, C. K. Johnson, C. Edwards, E. K. Matthews, D. Dolphin, and R. W. Boyle, J. Porphyrins Phthalocyanines, 2000, 4, 228-32. doi:

Advances in modern synthetic porphyrin chemistry, S. Shanmugathasan, C. Edwards, and R. W. Boyle, Tetrahedron, 2000, 56, 1025-46. doi:

Application of combinatorial techniques in the synthesis of unsymmetrically substituted 5,15-diphenylporphyrins, K. J. Elgie, M. Scobie, and R. W. Boyle, Tetrahedron Lett., 2000, 41, 2753-7. doi:

Mono-(pentafluorophenyl)porphyrins - Useful intermediates in the regioselective synthesis of multifunctionalised porphyrins, S. J. Shaw, K. J. Elgie, C. Edwards, and R. W. Boyle, Tetrahedron Lett., 1999, 40, 1595-6. doi:

Regioselective synthesis of multifunctionalised porphyrins - Coupling of mono-(pentafluorophenyl)porphyrins to electrophiles, S. J. Shaw, C. Edwards, and R. W. Boyle, Tetrahedron Lett., 1999, 40, 7585-6. doi:

Isothiocyanatoporphyrins, useful intermediates for the conjugation of porphyrins with biomolecules and solid supports, O. J. Clarke and R. W. Boyle, Chem. Commun., 1999, 2231-2. doi:

5-phenyldipyrromethane and 5,15-diphenylporphyrin, R. W. Boyle, C. Bruckner, J. Posakony, B. R. James, and D. Dolphin, in 'Organic Syntheses, Vol 76 - 1999', New York, 1999.

Selective synthesis of asymmetrically substituted 5,15-diphenylporphyrins, O. J. Clarke and R. W. Boyle, Tetrahedron Lett., 1998, 39, 7167-8. doi:

Novel and improved syntheses of 5,15-diphenylporphyrin and its dipyrrolic precursors, C. Bruckner, J. J. Posakony, C. K. Johnson, R. W. Boyle, B. R. James, and D. Dolphin, J. Porphyrins Phthalocyanines, 1998, 2, 455-65. doi:

5,10-Diphenyltripyrrane, a useful building block for the synthesis of meso-phenyl substituted expanded macrocycles, C. Bruckner, E. D. Sternberg, R. W. Boyle, and D. Dolphin, Chem. Commun., 1997, 1689-90. doi:

Porphocyanines: Expanded aromatic tetrapyrrolic macrocycles, L. Y. Xie, R. W. Boyle, and D. Dolphin, J. Am. Chem. Soc., 1996, 118, 4853-9. doi:

Hexadecafluorinated zinc phthalocyanine: Photodynamic properties against the EMT-6 tumour in mice and pharmacokinetics using Zn-65 as a radiotracer, R. W. Boyle, J. Rousseau, S. V. Kudrevich, M. O. K. Obochi, and J. E. vanLier, Br. J. Cancer, 1996, 73, 49-53. doi:

Structure and biodistribution relationships of photodynamic sensitizers, R. W. Boyle and D. Dolphin, Photochem. Photobiol., 1996, 64, 469-85. doi:

Synthesis of a Novel Water-Soluble Tetra[1-(O-Ethylphosphatobutyl)] Zinc Phthalocyanine, R. W. Boyle and J. E. Vanlier, Synthesis-Stuttgart, 1995, 1079-80. doi:

Iodination and Heck Alkynylation of 5,15-Diphenylporphyrin - a Convenient Entry to Asymmetrically Mesosubstituted Porphyrins, R. W. Boyle, C. K. Johnson, and D. Dolphin, J. Chem. Soc., Chem. Commun., 1995, 527-8. doi:

Peg-Coated Poly(Lactic Acid) Nanoparticles for the Delivery of Hexadecafluoro Zinc Phthalocyanine to Emt-6 Mouse Mammary-Tumors, E. Allemann, N. Brasseur, O. Benrezzak, J. Rousseau, S. V. Kudrevich, R. W. Boyle, J. C. Leroux, R. Gurny, and J. E. Vanlier, J. Pharm. Pharmacol., 1995, 47, 382-7. doi:

Meso-Phenyl Substituted Porphocyanines - a New Class of Functionalized Expanded Porphyrins, R. W. Boyle, L. Y. Xie, and D. Dolphin, Tetrahedron Lett., 1994, 35, 5377-80. doi:

A Convenient, One-Pot Synthesis of 1,9-Dicyano-Dipyrromethanes and a Difurylmethane, R. W. Boyle, V. Karunaratne, A. Jasat, E. K. Mar, and D. Dolphin, Synlett, 1994, 939-40. doi:

5,15-Diphenyl-7-Oxobenzochlorins - Novel Long-Wavelength Absorbing Photosensitizers for Photodynamic Therapy, R. W. Boyle and D. Dolphin, J. Chem. Soc., Chem. Commun., 1994, 2463-4. doi:

Biological-Activities of Phthalocyanines .13. The Effects of Human Serum Components on the Invitro Uptake and Photodynamic Activity of Zinc Phthalocyanine, M. O. K. Obochi, R. W. Boyle, and J. E. Vanlier, Photochem. Photobiol., 1993, 57, 634-40. doi:

Synthesis of Novel Water-Soluble Phthalocyanines for Use in the Photosensitized Inactivation of Cancer-Cells and Viruses, R. W. Boyle and J. E. Vanlier, Synlett, 1993, 351-2. doi:

Biological-Activities of Phthalocyanines .16. Tetrahydroxy - and Tetraalkylhydroxy Zinc Phthalocyanines - Effect of Alkyl Chain-Length on Invitro and Invivo Photodynamic Activities, R. W. Boyle, C. C. Leznoff, and J. E. Vanlier, Br. J. Cancer, 1993, 67, 1177-81. doi:

Biological-Activities of Phthalocyanines .14. Effect of Hydrophobic Phthalimidomethyl Groups on the Invivo Phototoxicity and Mechanism of Photodynamic-Action of Sulfonated Aluminum Phthalocyanines, R. W. Boyle, B. Paquette, and J. E. Vanlier, Br. J. Cancer, 1992, 65, 813-7. doi:

Biodistribution and Tumor Uptake of [Ga-67] Chlorogallium-Tetraoctadecyloxy Phthalocyanine and Its Sulfonation Products in Tumor-Bearing C3h Mice, J. Rousseau, R. W. Boyle, A. H. Maclennan, T. G. Truscott, and J. E. Vanlier, Nucl. Med. Biol., 1991, 18, 777-82. doi:

Sulfonated Phthalimidomethyl Aluminum Phthalocyanine - the Effect of Hydrophobic Substituents on the Invitro Phototoxicity of Phthalocyanines, B. Paquette, R. W. Boyle, H. Ali, A. H. Maclennan, T. G. Truscott, and J. E. Vanlier, Photochem. Photobiol., 1991, 53, 323-7. doi:

On the Nature of the Active Component of Hematoporphyrin Derivative .2, R. W. Boyle, W. F. Keir, A. H. Maclennan, G. Maguire, and T. G. Truscott, Cancer Lett., 1987, 38, 9-14. doi:

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